THIS PROJECT IS DIRECTED AT NEW METHODS FOR THE SYNTHESIS OF "CHIRALLY DEUTERATED AMINO ACIDS AND IS DESCRIBED IN DETAIL IN THE HIGHLIGHTS SECTION OF THIS REPORT. THE "CHIRALLY DEUTERATED" AMINO ACIDS ARE REQUIRED NMR ANALYSIS OF PROTEIN STRUCTURE. THE B-METHYLENE PROTONS FOUND IN FIFTEEN OF THE TWENTY COMMON AMINO ACIDS ARE DIASTEREOTOPIC. THEREFORE, THEY ARE CHEMICALLY INEQUIVALENT GIVING RISE TO A TIGHTLY COUPLED AB MULTIPLET IN THEIR PROTON NMR SPECTRUM. THUS SCALAR COUPLED RESONANCES ARE OBSERVED FOR EACH OF THE B-METHYLENE PROTONS EXACERBATING SPECTRAL CROWDING IN THIS REGION. THIS SPECTRAL CROWDING PROBLEM CAN BE SOLVED BY STEREOSELECTIVELY REPLACING THE PROS (OR PROR) PROTON WITH A DEUTERON EFFECTIVELY ELIMINATING HALF OF THE B-METHYLENE PROTON RESONANCES AND INCREASING THE INTER PROTON DISTANCE. IN ADDITION, CHIRAL SUBSTITUTION OF THE PRO-CHIRAL METHYLENE PROTONS WOULD PROVIDE AN UNEQUIVOCAL METHOD FOR MAKING STEREOCHEMICAL ASSIGNMENTS TO THESE PROTON RESONANCES. SIMILAR TO THE DIASTEREOTOPIC HYDROGENS AT THE B-CARBON, VALINE AND LEUCINE HAVE DIASTEREOTOPIC METHYL GROUPS. DIFFERENTIAL 2H LABELING OF THESE METHYL GROUPS WILL REDUCEIN HALF THE NUMBER OF RESONANCES IN A CROWDED METHYL REGION OF THE SPECTRUM AND PROVIDE UNEQUIVOCAL STEREOCHEMICAL ASSIGNMENTS OF T HE METHYL RESONANCES. THIS PROJECT HAS DEVELOPED METHODS FOR DEUTERATING DIASTEREOTOPIC B-METHYLENE PROTONS AND DIASTEREOTOPIC METHYL GROUPS IN AMINO ACIDS. OPPOLZER'S CAMPHOR SULTAM CHIRAL AUXILIARY WAS USED TO INDUCE THE STEREOCHEMISTRY AT THE B-CARBON.